AT339326B - Verfahren zur herstellung von 1,8-naphthyridin -3- carbonsauren - Google Patents
Verfahren zur herstellung von 1,8-naphthyridin -3- carbonsaurenInfo
- Publication number
- AT339326B AT339326B AT1032474A AT1032474A AT339326B AT 339326 B AT339326 B AT 339326B AT 1032474 A AT1032474 A AT 1032474A AT 1032474 A AT1032474 A AT 1032474A AT 339326 B AT339326 B AT 339326B
- Authority
- AT
- Austria
- Prior art keywords
- naphthyridine
- methyl
- dihydro
- oxo
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- 125000005270 trialkylamine group Chemical group 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- -1 substituted Chemical class 0.000 claims description 3
- 125000004954 trialkylamino group Chemical group 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- XFNNRAPTEMICAG-UHFFFAOYSA-M [I-].C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(=O)C[N+]1=CC=CC2=CC=CC=C12 Chemical compound [I-].C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(=O)C[N+]1=CC=CC2=CC=CC=C12 XFNNRAPTEMICAG-UHFFFAOYSA-M 0.000 claims 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000013078 crystal Substances 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- MHWLWQUZZRMNGJ-UHFFFAOYSA-N nalidixic acid Chemical compound C1=C(C)N=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 MHWLWQUZZRMNGJ-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 10
- 238000009835 boiling Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- LSUQPHPXYPEBRM-UHFFFAOYSA-N 3-(2-bromo-2-methylpropanoyl)-1-ethyl-7-methyl-1,8-naphthyridin-4-one Chemical compound C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(C(C)(C)Br)=O LSUQPHPXYPEBRM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- WIZNBODWFXTVAP-UHFFFAOYSA-N 1-ethyl-7-methyl-3-(2-methylpropanoyl)-1,8-naphthyridin-4-one Chemical compound C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(C(C)C)=O WIZNBODWFXTVAP-UHFFFAOYSA-N 0.000 description 1
- ZPVXFTFVNMMWJX-UHFFFAOYSA-N 1-ethyl-7-methyl-3-(3-phenylpropanoyl)-1,8-naphthyridin-4-one Chemical compound C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(CCC1=CC=CC=C1)=O ZPVXFTFVNMMWJX-UHFFFAOYSA-N 0.000 description 1
- CYDFIAGFVIGXQJ-UHFFFAOYSA-N 1-ethyl-7-methyl-3-propanoyl-1,8-naphthyridin-4-one Chemical compound CC1=CC=C2C(=O)C(C(=O)CC)=CN(CC)C2=N1 CYDFIAGFVIGXQJ-UHFFFAOYSA-N 0.000 description 1
- FSRVQSSHFLOXGR-UHFFFAOYSA-M 1-ethylpyridin-1-ium;iodide Chemical compound [I-].CC[N+]1=CC=CC=C1 FSRVQSSHFLOXGR-UHFFFAOYSA-M 0.000 description 1
- IMNUYXFNLOVWEF-UHFFFAOYSA-N 3-(2-cyclohexylacetyl)-1-ethyl-7-methyl-1,8-naphthyridin-4-one Chemical compound C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(CC1CCCCC1)=O IMNUYXFNLOVWEF-UHFFFAOYSA-N 0.000 description 1
- XAAMWTVILCMENA-UHFFFAOYSA-M 3-[1-(cyclohexylmethyl)pyridin-1-ium-2-carbonyl]-1-ethyl-7-methyl-1,8-naphthyridin-4-one iodide Chemical compound [I-].C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(=O)C1=[N+](C=CC=C1)CC1CCCCC1 XAAMWTVILCMENA-UHFFFAOYSA-M 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QUXLCYFNVNNRBE-UHFFFAOYSA-N 6-methylpyridin-2-amine Chemical compound CC1=CC=CC(N)=N1 QUXLCYFNVNNRBE-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- XZOVCSPCZQGKJD-UHFFFAOYSA-N C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(CCC1CCCCC1)=O Chemical compound C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(CCC1CCCCC1)=O XZOVCSPCZQGKJD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- OTBBVGDVKUGFQK-UHFFFAOYSA-M [Br-].C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(=O)C1=C(C(=[N+](C=C1)C)C)C Chemical compound [Br-].C(C)N1C=C(C(C2=CC=C(N=C12)C)=O)C(=O)C1=C(C(=[N+](C=C1)C)C)C OTBBVGDVKUGFQK-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49007185A JPS514197A (en) | 1973-12-29 | 1974-01-16 | 1** nafuchirijinjudotaino seizoho |
| HU74CI00001522A HU171869B (hu) | 1974-01-17 | 1974-12-05 | Novyj sposob poluchenija proizvodnykh 1,8-naftiridina |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ATA1032474A ATA1032474A (de) | 1977-02-15 |
| AT339326B true AT339326B (de) | 1977-10-10 |
Family
ID=26318404
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT1032474A AT339326B (de) | 1974-01-16 | 1974-12-27 | Verfahren zur herstellung von 1,8-naphthyridin -3- carbonsauren |
Country Status (2)
| Country | Link |
|---|---|
| AT (1) | AT339326B (pl) |
| PL (1) | PL95842B1 (pl) |
-
1974
- 1974-12-27 AT AT1032474A patent/AT339326B/de not_active IP Right Cessation
-
1975
- 1975-01-15 PL PL17734775A patent/PL95842B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL95842B1 (pl) | 1977-11-30 |
| ATA1032474A (de) | 1977-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ELJ | Ceased due to non-payment of the annual fee |